Should You Claim Social Security While Still Working?
Should You Claim Social Security While Still Working?
February 6, 2025
February 6, 2025

In today’s mailbag episode, we’re answering a question from Bobby about Social Security. He plans to keep working for another two years but wonders if he should start taking his benefits now since he’s reached full retirement age. Is it a smart move, or could waiting be a better strategy?

While everyone’s situation is unique, Frank will share how he helps clients determine the right time to start claiming benefits. Tune in to hear Frank’s insights, key factors to consider, and how timing your benefits could impact your long-term financial security.


Here’s what we discuss in this episode:

0:00 – Intro

0:53 – Tax implications of taking Social Security early

1:47 – How Frank helps clients answer this question

Subscribe & follow the show for free on your favorite apps:

Helpful Resources:

Learn more about the T.I.M.E. planning process by clicking here.


You can also schedule a free planning session with Frank Oliver and the team by clicking here.

Get your copy of Frank's book!

March 20, 2025
Many retirees and pre-retirees dream of owning a vacation home that they can visit throughout the year. But if you decide to make this move, how should you go about financing a second property? That’s the question one of our listeners, Ted, asked Frank this week.
By Walter Storholt March 13, 2025
We've got a great listener question for you today! This week, Barry shares that he has a life insurance policy through his job, as well as a whole life policy he purchased several years ago. Now, he’s wondering- does he really need both, or should he consider canceling one?
By Walter Storholt March 6, 2025
Social Security claiming strategies can vary greatly depending on family dynamics. This episode explores how different family situations, such as those with a stay-at-home spouse or a blended family, could impact when and how to claim Social Security benefits to help maximize your retirement income.
February 25, 2025
Retirement accounts and divorce
February 25, 2025
Why do you need a financial advisor?
By Walter Storholt February 20, 2025
In today’s video, Rebecca asks an important question about retirement planning: With four different investment accounts- her 401(k), IRA, Roth IRA, and individual account- she’s wondering which one she should withdraw from first when she retires next year and needs income.
By Walter Storholt February 13, 2025
Financial mistakes can happen at any age, but they can have a particularly significant impact in your 60s. In today’s episode, Frank discusses 5 common financial blunders to avoid during this pivotal decade.
financial resolutions
By Walter Storholt January 30, 2025
We've got some financial changes that'll help you out and some new mindsets and mentalities that'll put you in the right direction as you go through the new year.
By Walter Storholt January 23, 2025
A listener recently reached out, sharing that their house feels like a constant money pit. They're dealing with one repair after another, and the cost and effort are leaving them frustrated. They’ve asked Frank if he thinks it would be a bad idea to sell the house and rent while they figure out their next move.
January 22, 2025
Why do you need a tax professional?
Show More
Share by: